Download PDF
Synthesis 2004(4): 506-508  
DOI: 10.1055/s-2004-815961
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

A Rapid and Efficient Synthesis of 2-Butyl-5-Chloro-3H-Imidazole-4-Carboxaldehyde

K. Srinivas*, C. K. Snehalatha Nair, S. Ramesh, M. Pardhasaradhi
Specialty Gas Based Chemicals & Processes Division, FCL Lab, Indian Institute of Chemical Technology, Hyderabad 500 007, India
e-Mail: kantevari@yahoo.com;
Further Information

Publication History

Received 22 December 2003
Publication Date:
09 February 2004 (online)

    Permissions and Reprints All articles of this category

Abstract

A rapid, efficient, cost effective procedure has been developed for the synthesis of 2-butyl-5-chloro-3H-imidazole-4-carboxaldehyde. Preparation of methyl pentanimidate was accomplished in just 12 hours, followed by a sequence of reactions without isolation and purification of the formed intermediates. The final compound was purified by simple acid-base treatment to get a product with 99.9% HPLC purity.

Key words

imidazole - imidates - Vilsmeier reagents - nitrile - tetrazole

    References

  • 1 Duncia JV. Carini DJ. Chiu AT. Pierce ME. Smith RD. Wells GJ. Wang PC. Wexier PR. Johnson AL. Timmermans PBMWM. Drugs Fut.  1991,  16:  305 
    CrossrefSearch in Google Scholar
  • 2 Carini DJ. Duncia JV. Aldrich PE. Chiu AT. Johnson AL. Pierce ME. Price WA. Santella JB. Wells GJ. Wexler RR. Wong PC. Yoo SE. Timmermans PBMWM. J. Med. Chem.  1991,  34:  2525 ; and references reported therein
    CrossrefSearch in Google Scholar
  • 3 Scrip  1994,  1963:  23 
  • 4 Takeda Chemical Industries Ltd. . inventors; JP  5798270.  ; Chem. Abstr. 1983, 98, 4543a
  • 5 Yamamoto T, Hibi Y, and Ogawa T. inventors; US Patent  5395943. 
  • 6 Elz S. Kramer K. Pertz HH. Detert H. Laak AK. Kuhne R. Schunack W. J. Med. Chem.  2000,  43:  1073 
    Search in Google Scholar
  • 7 Furukawa Y, Kishimoto S, and Nishikawa K. inventors; US Patent  4355040. 
  • 8 Basappa MPS. Mantelingu K. Swamy SN. Rangappa KS. Bioorg. Med. Chem.  2003,  11:  4539 
    CrossrefSearch in Google Scholar
  • 9 Pardhasaradhi M, Srinivas K, and Snehalatha Nair CK. inventors; US patent  6326498.  ; Chem. Abstr. 2001, 136, 5996
  • 10 Srinivas K. Snehalatha Nair CK. Ramesh S. Pardhasaradhi M. Org. Prep. Proced. Int.  2003,  35:  537 
    Search in Google Scholar
  • 11 Dzurion P. Schunarck W. Arch. Phamazie  1974,  307:  470 
    Search in Google Scholar
  • 12 Shi Y.-J. Frey LF. Tschaeu DM. Verhoeven TR. Synth. Commun.  1993,  23:  2623 
    CrossrefSearch in Google Scholar
  • 13 Griffiths GJ. Chimia  1997,  51:  283 
    Search in Google Scholar
  • 14 Griffiths GJ. Hauck MB. Imwinkelried R. Kohr J. Roten C. Stucky GC. J. Org. Chem.  1999,  64:  8084 
    CrossrefSearch in Google Scholar
  • 15 Pardhasaradhi M, Srinivas K, Snehalatha Nair CK, and Ramesh S. inventors; Indian Patent  NF132.